Since I began offering what amounts to be a “comedy writing for salespeople” training & workshop, people react to what I offer the same way they do to a new Star Wars trailer: thrilled and confused. In short, I want sales reps to simultaneously obtain their prospects' attention, and show a grasp of their challenges. Let’s kick things off with a quote:

“Insanity is doing the same thing over and over again and expecting different results” -Albert Einstein

If Einstein was around today, his LinkedIn profile’s tagline would read “Influential Thought Leader In Stuff You Don’t Understand”. However I disagree with Einstein, as I’d change “insanity” in the above quote with “stupidity”. Though, in his defense, he invented a theory of relativity, while I struggle to score likes & shares on LinkedIn. If he was around today, he’d have reverse-engineered LinkedIn’s algorithm while trimming his moustache and be in fact a leading influencer. The irony is that the solution to my own problem is to post something antagonistic on LinkedIn like “Me: Smarter than Einstein. Fo’ Realz, YO!” (nothing like sowing the seeds of outrage to drive interest in your own brand, but I digress).

So many potentially fruitful businesses or ideas within businesses are burned to the ground because of incompetence, greed, ego, and a lack self-awareness. So much innovative thought & morale are tossed into metaphorical bonfires because leadership doesn’t have the will or desire to fix basic problems. So, it’s hilarious when leaders make the same mistakes over and over again. Except when they’re our bosses. Then it’s tragic.

“Comedy = tragedy + time” - Steve Allen

This equation is far more meaningful to me than anything that know-it-all Einstein ever proved. Back in 1937, Hindenburg jokes were taboo, but today, it’s a metaphor for disaster. Yet, in the business world, struggling through hard times just to someday laugh about them is neither a payoff nor an option. Repeated insanity experienced by employees in the present, is an utter tragedy, which not only affects profitability, but also diffuses morale and lower productivity. Ominous stuff. Nothing says “hilariously good times” like mass layoffs.

Good salespeople are like psychiatrists. We let prospects traumatized by operational frustrations vent their problems in a forum we offer them. Our role is to listen and prescribe the right medication to cure the patient, and get them back to a healthy operational state. That said, the first step in asking for help, is knowing it’s needed. Part of our role is to help our prospect admit (or see) that they need to open up to us. To do that, we need to:

1) Get their attention;

2) Display empathy;

3) Be respected & liked.

On the other hand, stand-up comedians are the ultimate attention-getters. We seek buy-in from their audience because we speak about relatable challenges/observations, and frame them in a way that drives engagement. And like the comedian, sales reps need to achieve this quickly. Attention spans are shorter than ever. Whether it’s on a cold call, or during a demo/sales pitch, a well-crafted, well-placed joke can do it all in a couple of short sentences.

Consider the following, which I crafted for an employee at a company that sells pre-built predictive analytics tools to clothing retailers – everyday, comedic fodder. Test yourself, and deliver it out loud. Imagine you’re onstage and need to project, and deliver with some charisma:

Clothing retailers are building their own predictive analytics tools in order to make more informed decisions, but building software is not core business. That’d be like if Oracle opened a “Big and Tall” shop.

I know, I know: too soon. This joke will not be appreciated by everyone, but it doesn’t care. It wasn’t written for comedy club or my Netflix special. It’s for a very specific audience – the vendor’s prospects. Helping prospects laugh about their problem can become their first step in fixing it. Such jokes show the prospect that the rep understands a challenge they face, their industry, and it should get the prospect to – at the very least – crack a smile and crawl onto the couch for deep therapy.

If you're in Montreal, check out my therapy most Sundays at my weekly stand-up show in Montreal: ComedyAbroad.com/MTL